Alice Tompkins

Alice Tompkins is Jay Sherman's girlfriend who lives in New York as a single parent with Penny Tompkins. Alice is originally from Tennessee where she speaks with a strong Southern accent.

Plot
Alice is introduced in the second season episode " Sherman, Woman and Child " and is named after Alice Kramden from The Honeymooners. She has a younger brother named Bisquick and an older sister named Miranda who's name sake is from William Shakespeare’s The Tempest, completing the siblings gag on being named after a sitcom character, a character from a play and a pancake batter mix. She was once married to a country singer, Cyrus Tompkins, but she left him when she began to suspect he was cheating on her (she reached this conclusion after seeing Cyrus' new album, entitled "I'm Being Unfaithful to My Wife, Alice Tompkins. You Heard Me, Alice Tompkins" ).

Alice was once an artist and is still capable of painting, she is extremely talented being able to make perfect replicas of masterworks on the walls of her apartment (such as Michelangelo ‘s The Creation of Adam and Georges-Pierre Seurat ’s A Sunday Afternoon on the Island of La Grande Jatte ). She pepper-sprayed Jay Sherman upon first meeting him on the street, an act he shrugged off (and even enjoyed). She accepted Jay's offer to work as his personal assistant. In the episode " Lady Hawke ", she realized she had fallen in love with him and the two become a couple.

Alice's daughter Penny quickly takes a liking to Jay, initially calling him "funny man" due to his comic mishaps. Later in the season she begins to call him "Uncle Jay." When Jay and Alice are unable to get Penny admitted into any of the top preschools, Jay's boss, Duke Phillips, founds one exclusively for her, staffed by Jimmy Breslin , Sean Young and Prince Charles.

A fifth tagline for the closing credits was created to go with the original four. In this scene, Jay and Alice are kissing in the theater seats as the credits roll and they are interrupted by an usher.

In the first Critic webisode, Jay's makeup artist Jennifer asks him what happened to his self-esteem, to which Jay replies that he lost it in the second divorce settlement. Although Alice is not mentioned by name, this led many fans to believe that Jay and Alice had married and eventually ended up in a bitter divorce. Despite this belief, the fate of Alice is left unknown as his second divorce was technically from a Mexican airport employee who he married in the episode " Marty's First Date ." In either case, the fact that Jay is now romantically pursuing another woman (Jennifer) implies that he and Alice are no longer in a relationship.